Synthesis of nucleoside-amino acid conjugates containing boranephosphate, boranephosphorothioate and boranephosphoramidate linkages |
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Authors: | Janina Baraniak Renata Kaczmarek Ewa Wasilewska |
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Institution: | Department of Bioorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 ?ód?, Poland |
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Abstract: | Conjugates of 3′-azido-2′,3′-dideoxythymidine (AZT) and 2′,3′-didehydro-2′,3′-dideoxythymidine (D4T) with the hydroxyl group of tyrosine containing boranephosphate and boranephosphorothioate moieties were prepared via the oxathiaphospholane and dithiaphospholane methodology as a mixture of P-diastereomers. Their structures were confirmed by MS analysis and 1H, 31P NMR spectroscopy. It has been shown that the boranephosphorothioate linkage is unstable under acidic conditions. The first nucleoside-alanine conjugates connected through a boranephosphoramidate linkage were also obtained. |
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Keywords: | Nucleoside Amino acids Conjugates Prodrugs Boranephosph(orothio)ate Boranephosphoramidate Oxathiaphospholane chemistry |
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